A new β-carboline alkaloid from the seeds of Griffonia simplicifolia

Chin J Nat Med. 2013 Jul;11(4):401-5. doi: 10.1016/S1875-5364(13)60059-X.

Abstract

Aim: To study the chemical constituents from the seeds of Griffonia simplicifolia Baill.

Methods: The chemical constituents were isolated and purified by a combination of chromatographic materials including silica gel, Sephadex LH-20, and preparative TLC. Their structures were elucidated on the basis of MS and NMR data analysis. The cytotoxic activities were evaluated against HepG2 cancer cell line using the MTT colorimetric method.

Results: A new β-carboline alkaloid, griffonine (1), together with seven known alkaloids, hyrtioerectine B (2), 3-carboxy-6-hydroxy-β-carboline (3), hyrtiosulawesine (4), 5-hydroxyindole-3-carbaldehyde (5), 5-hydroxy-3-(2-hydroxyethyl) indole (6), trigonelline (7), and 5-hydroxytryptamine (8) were isolated and identified. Alkaloids 1, 2 and 4 showed growth inhibitory effects on the HepG2 cell line with IC50 values of 23.5, 9.6 and 19.3 μmol·L(-1), respectively.

Conclusion: Alkaloid 1 is new and was named griffonine. Alkaloids 2-7 were isolated from this plant for the first time. Alkaloids 1, 2 and 4 were potentially cytotoxic.

Keywords: Alkaloids; Cytotoxicity; Griffonia simplicifolia seeds; New β-carboline alkaloid.

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology
  • Carbolines / chemistry*
  • Carbolines / isolation & purification
  • Carbolines / pharmacology
  • Cell Proliferation / drug effects
  • Griffonia / chemistry*
  • Hep G2 Cells
  • Humans
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Seeds / chemistry

Substances

  • Alkaloids
  • Carbolines
  • Plant Extracts